Sodium Hydroxide → HCID 67173666, compound

HRID 570174Notes

Reaction equation

HRID 570174 reaction equation
C[O:2][C:3](=[O:29])[CH2:4][C@@H:5]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:9]2[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:8]=2[N:7]2[C:25]([CH3:28])=[N:26][N:27]=[C:6]12.[OH-].[Na+]>C1COCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[C:9]3[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:8]=3[N:7]3[C:25]([CH3:28])=[N:26][N:27]=[C:6]3[C@H:5]([CH2:4][C:3]([OH:29])=[O:2])[N:11]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 52936135HCID 52936135, compound

Product 1

HCID 67173666HCID 67173666, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Methyl[(4S)-6-(4-chlorophenyl)-1-methyl-8-(methyloxy)-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetate (for a preparation see Reference compound G) (7.4 g, 18.1 mmol) in THF (130 mL) at room temperature was added 1N NaOH (36.2 mL, 36.2 mmol). The reaction mixture was stirred at this temperature for 5 h before being quenched with 1N HCl (36.2 mL) and concentrated in vacuo. Water is then added and the aqueous layer was extracted with DCM (×3) and the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure to give the title compound (7 g, 98% yield) as a pale yellow solid.

Workup

  1. customat room temperature
  2. custombefore being quenched with 1N HCl (36.2 mL)
  3. concentrationconcentrated in vacuo
  4. additionWater is then added
  5. extractionthe aqueous layer was extracted with DCM (×3)
  6. dry with materialthe combined organic layers were dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9dd9835dd5c44ec6b84803e1f7dddf51
Source dataset
uspto-grants-2015_05
Patent number
US09023842B2

Reaction notes

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